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According to "Hewn from Courage: The History of Springfield", Jebediah Springfield was born in Axhandle, Virginia in 1774, the twelfth of seventeen children. His father Ned Springfield was a farmer who introduced yellow Eurasian late-summer squash to Eastern Virginia. While yellow Eurasian late-summer squash no longer grows in the part of the country, the yellow Eurasian late-summer squash beetle, one of nature's hungriest pests, is still around to remind us of Mr. Springfield's foresight. Little is known of Jebediah's mother Olive Springfield, except that she was very pretty and very busy. Young Jebediah, like most children who grow up to be great heroes, was a hard-working student who always treated his elders with much respect. He did his homework by candlelight and never "imitated bodily noises in class or taped naughty pictures to the classroom screen". Young Jebediah had one dream: To go west and explore the great American frontier.

At age 13, Jebediah had to leave school, which made him very sad. Searching for calling in life, he tried to help his father on the farm with his twelve brothers, but found that he was allergic to soil. Jebediah then went to work in a shop that printed fishing almanacs. He later wrote his own pamphlets, such as "The Curative Powers of Cigar Smoke" and "How to Write Pamphlets for Fun and Profit," but in the end, he could not ignore his passion for the frontier.[1]

Jebediah Springfield led a band of wagons from Maryland and headed westward with his partner Shelbyville Manhattan on a quest to find "New Sodom" after misinterpreting a passage of the Bible. They later parted over political differences; Manhattan wanted to found a town where people could marry their own cousins, while Springfield wanted a town devoted to chastity, abstinence, and a flavorless mush he called "root-marm". Manhattan went on to found the rival town of Shelbyville.

Despite Springfield's hero status in modern-day Springfield many of his famed deeds have come into question under historical examination. On an expedition to Springfield's historic "Fort Springfield", Bart uncovered inconsistencies in the Jebediah legend, discovering that he accomplished multiple heroic feats on the same day in different and far apart locations.

Lisa later proved that "Jebediah Springfield" was in fact a bloodthirsty pirate and enemy of George Washington named Hans Sprungfeld, who had changed his name in 1795 to hide his identity. He wrote his confession on a scrap of paper that formed the "missing piece" of the famously incomplete portrait of George Washington, which he procured when he stepped on the original painting while it was still wet.[2] However, upon seeing the town pride Springfield has for their founder and history, Lisa decided to keep the discovery to herself.

A distinguishing characteristic of Sprungfeld was his prosthetic silver tongue, which was built to replace his real tongue which was bitten off by a Turkish pirate during a grog house fight. According to The Simpsons Guide to Springfield rumors state that the silver tongue is currently in the possession of Mayor Quimby, who uses it as a paperweight.

Springfield is said to have dramatically killed a bear with his bare hands, though revisionist historians have determined the bear in fact probably killed him.[3] A statue depicting Springfield's victory stands in the center of the Springfield town square, in front of the city hall. His secret will contains a confession that he was suffering from then fatal diphtheria and according to Lisa Simpson's research, he died of syphilis. The will also reveals that the untameable buffalo he was believed to have tamed was already tame and that he merely shot it.[4] According to Bart, he may have been shot by Indians after the townspeople traded guns for corn but the Indians shot them and took the corn.

The statue was once beheaded with a hacksaw by Bart, who thought that it would make him more popular. In reality, the town became depressed and angry, leaving Bart to endure “The Tell-Tale Heart”-style guilt before he returned the head to its rightful place.[5] It appears that while the head is back in its rightful place it has never been properly re-attached, as it frequently falls off.